Fashion·9 min read

What To Wear on Chill Weekends That Doesn’t Make You Look Sloppy

chill-weekend-header
Design: theSkimm | Photos: FP Movement, Gap, Aritzia
September 11, 2026

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Whether a chill weekend to you is running errands or one social engagement then staying home (we get it), these outfits will make you feel put-together without skimping on comfiness. Maybe beauty doesn’t have to be pain.

For more affordable, stylish outfit ideas, click here.

pullover

FP Movement

Restoration Yarn Dye Stripe Layer

A striped pullover you’ll never get tired of…

Stripes have always been cool; add the mock neck and you have a pullover you’ll get excited to reach for. It’s made of 100% cotton, so you know it’ll be comfy, and it pairs nicely with our favorite capri leggings

gap-pants

Gap

Easy Wide-Leg Pants

A pair of pull-on pants that look polished…

These are like the sweatpants you lounge around in, but they have a slightly more tailored fit and are made of twill fabric that gives them a dressy vibe. Throw on a tee and sneakers for casual days or dress them up with heels for date night. 

quince-sweater

Quince

Mongolian Cashmere Crewneck Sweater

A cashmere sweater that only looks expensive…

You can’t go wrong with a cashmere crewneck sweater. Whether you throw it on over a tank or tie it around your shoulders, it makes your outfit look intentional. This one is soft, not too oversized, and comes in a wide range of colors. 

cardigan

Abercrombie & Fitch

Sunday Shrunken Cardigan

A cardigan that feels like a worn-in sweatshirt…

This cardigan is made of the same fabric as their sweatshirts, so you know it’ll feel like a dream as you’re running around. It’s layerable and goes great with the matching wide-leg sweatpants

sweatpant-jeans

Rag & Bone

rb Miramar Wide-Leg Pant

The iconic Rag & Bone sweatpant jeans…

Rarely do we recommend spending this much on casual clothes, but when it comes to the sweatpant jeans, they’re actually worth it. They look like real wide-leg jeans — in either light or dark wash — but are made of soft cotton terry. We love wearing them when we’re traveling. 

rugby

Aritzia

Mighty Cotton™ Lomu Polo

A rugby polo you can dress up or down…

One editor’s errands outfit du jour always includes this striped rugby polo. It’s made of the most delicious-feeling heavyweight cotton, which is perfect for brisk mornings, and it gives any outfit a cool, sporty vibe. Each colorway is better than the last. 

capris

FP Movement

Never Better Mini Leggings

Easy-to-style capri pants…

These capri leggings are much easier to style than you might fear. They’re chic with flip-flops, ballet flats, and sneakers alike. They also happen to be the most comfortable leggings we own, length notwithstanding. The material is ridiculously soft and has some substance to it (so you can get away with wearing them as real pants), and they offer the gentlest compression that doesn’t feel restrictive. 

hoodie

Gap

VintageSoft Zip Hoodie

The only zip-up hoodie you need…

Whether you pair it with jeans or joggers, this hoodie looks retro and polished, especially when you pair it with a white tank underneath. It has fleece on the inside, so it’ll actually keep you warm if it’s chilly outside. 

tee

Old Navy

EveryWear Long-Sleeve T-Shirt

A long-sleeve tee for every day…

In this house, we love a long-sleeve tee; it’s the perfect transitional staple. This one isn’t too fitted, goes great with jeans, and even comes in tall or petite options if you need a specific length. 

levis

Levi's

Low Loose Jeans

A pair of low-rise jeans we can’t stop wearing…

We’ve talked about these jeans before, and we’ll talk about them again. They hit just below your belly button, so you don’t have to worry about showing too much. Plus, they’re less baggy than other pairs, making them appropriate for casual offices. They’re one of the comfiest pairs we own. 

lululemon

Lululemon

Breezily Mid-Rise Pant

A pair of active pants that are chicer than most…

Swish through your day in these lightweight, sweat-wicking, casual pants. They have a good amount of stretch and a mid-rise elastic waistband. Plus, they have a hidden card pocket if you want to leave your bag at home.

cargo-pants

Pilcro

Cade 100% Cotton Low-Slung Cargo Pants

Cargo pants that look like trousers…

These pants are low-slung and relaxed, but they don’t look like all you’re missing is your utility belt for a day on the job. They’re 100% cotton, so they wear well in any season, and they have an adjustable drawstring waistband. 

buck-mason

Buck Mason

Field-Spec Boyfriend Crop Tee

A just-right tee…

The key to a good off-duty look is a tee that fits perfectly. This one is made of a nice heavyweight cotton that already feels lived in. It’s boxy (but not in a bad way) and cropped, so you can show off your favorite jeans. 

asics

Asics

GT-2160 Sneakers

A pair of editor-loved sneakers…

These Asics are incredibly supportive without being too cushiony. We love them for daily walks, and they even helped resolve joint and foot pain for one of our editors. They also just look cool, whether you’re wearing athletic gear or jeans. We love them so much, we gave them a Good for You Award

hat

Favorite Daughter

The Script Logo Baseball Cap

A new version of the baseball cap we wear all the time…

We’ve written about this Favorite Daughter cap before, but this new version is somehow even cheekier. We love the bright red color and the retro-looking font. Wear it whether you’re the favorite daughter or the only daughter. 

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